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Au-Catalyzed Cyclization of Monopropargylic Triols: An Expedient Synthesis of Monounsaturated Spiroketals

Aaron Aponick*, Chuan-Ying Li and Jean A. Palmes

*Department of Chemistry, University of Florida, Gainesville, Florida 32611, Email: aponickchem.ufl.edu

A. Aponick, C.-Y. Li, J. A. Palmes, Org. Lett., 2009, 11, 121-124.

DOI: 10.1021/ol802491m (free Supporting Information)


Abstract

A cyclization of monopropargylic triols to form olefin-containing spiroketals is rapid and high yielding in the presence of 2 mol % of a catalyst generated in situ from Au[P(t-Bu)2(o-biphenyl)]Cl and AgOTf. Various substituted triols lead to substituted 5- and 6-membered ring spiroketals.

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Key Words

Acetals, Lactols


ID: J54-Y2009-0080